186586-84-5Relevant academic research and scientific papers
A radical cyclisation based cyclopentenone annulation of allyl alcohols
Srikrishna,Viswajanani,Sattigeri
, p. 2975 - 2983 (2007/10/03)
A four-step cyclopentenone annulation reaction of allylic alcohols employing a 5-exo-trig radical cyclisation reaction of mixed allyl methyl ketals of bromoacetone as the key step is described. The annulated product 12b obtained from 2,3-dimethylcyclohexenol has been further elaborated into (±)-epibakkenolides employing a 5-exo-dig radical cylisation reaction based α-spiro-β-methylene-γ-butyrolactone annulation methodology.
Generation and synthetic application of metallated methyl isopropenyl ether, a substitute for acetone enolate
Taherirastgar, Foroogh,Brandsma, Lambert
, p. 45 - 48 (2007/10/03)
Methyl isopropenyl ether (1) has been metallated at low temperature with a 1:1 molar mixture of n-BuLi/t-BuOK in THFhexane, and subsequently functionalized with a variety of electrophilic reagents. At temperatures higher than -30°C, the metallated methyl isopropenyl ether (2) decomposes with formation of allene. When the suspension of 2 is allowed to warm up to room temperature in the presence of an additional equivalent of n-BuLi, the intermediary aliene is converted into 1-propynyllithium (2c), which reacts with propyl thiocyanate to give 1-propylthio-1-propyne (4). Some of the functionalization products were subjected to acidic hydrolysis affording the expected methyl ketones. VCH Vcrlagsgescllschaft mbH.
Cyclopentaannulation of Allyl Alcohols via a Radical Cyclisation Reaction. Total Synthesis of 4-Epibakkenolide-A
Srikrishna, A.,Viswajanani, R.,Sattigeri, J. A.
, p. 469 - 470 (2007/10/02)
A four step cyclopentaannulation methodology starting from allyl alcohols using 5-exo-trig radical cyclisation as the key reaction, and its application to the total synthesis of 4-epibakkenolide is described.
